Processes Utilizing An Organic Solvent Or A Compound Having Alcoholic Hydroxy Bonded Directly To An Acyclic Carbon, Or Product Thereof Patents (Class 530/507)
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Publication number: 20110313141Abstract: There is described a method of processing biomass which comprises the digestion of biomass material in an aqueous solvent system subjected to ultrasonic waves and separating the biomass into its constituents of lignin, hemicellulose and cellulose. There is also described a system for the processing of biomass which comprises the digestion of biomass material in an aqueous solvent system subjected to ultrasonic waves and separating the biomass into ins constituents of lignin, hemicellulose and cellulose.Type: ApplicationFiled: November 23, 2009Publication date: December 22, 2011Applicant: BIO-SEP LIMITEDInventor: Stephen Brooks
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Patent number: 8053566Abstract: Lignin polymers having distinctive properties, including a generally high molecular weight and generally homogeneous size distribution, as well as preservation of native reactive side groups, are isolated by solvent extraction of plant materials. Methods for isolation of lignin polymers, and for use of the isolated lignin polymers are disclosed. Compositions containing lignin isolated from plant materials, such as carbon fiber composites, resins, adhesive binders and coatings, polyurethane-based foams, rubbers and elastomers, plastics, films, paints, nutritional supplements, food and beverage additives are disclosed. Xylose and xylose derivatives, furfural, fermentable sugars, cellulose and hemi-cellulose products may be used directly or further processed. The lignin polymers and other plant-derived products disclosed herein may be produced in abundance at low cost, and may be used as substitutes for feedstocks originating from fossil fuel or petrochemical sources in the manufacture of various products.Type: GrantFiled: September 2, 2008Date of Patent: November 8, 2011Assignee: Vertichem CorporationInventors: Helene Belanger, Ross L. Prestidge, Tony James Lough, James D. Watson
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Publication number: 20110160442Abstract: The invention relates to a method for the fractionation of knotwood extract, which has been obtained by extraction of knotwood with a hydrophilic solvent. The hydrophilic extract is extracted with a lipophilic solvent to remove lipophilic impurities. The invention also relates to the use of a liquid-liquid extraction for the purification of hydrophilic knotwood extract. The present process provides a purified knotwood extract, which contains more than 90% lignans, flavonoids and stilbenes and less than 10% impurities selected from resin acids, fatty acids, sterols, juvabiones, triglycerides and combinations thereof.Type: ApplicationFiled: June 18, 2009Publication date: June 30, 2011Inventors: Suvi Pietarinen, Ulf Hotanen
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Publication number: 20110129886Abstract: Non-food plant biomass is subjected to hot-water extraction in a pressurized vessel at an elevated temperature up to about 250° C. and at a pH below about 7.0, to yield an aqueous extract containing hemicellulosic components, other wood-derived compounds, and a lignocellulosic residue. The separated aqueous extract or liquor is purified and concentrated through a multi-step process producing fermentable sugars. At each stage, inhibitory chemicals such as acetic acid, lignin, and furfural are separated and eventually recovered as commercial chemicals. The lignocellulosic residue may be further processed, as a material with enhanced resistance to sorption of water, for manufacture of improved pulp and paper, construction materials, pellet fuel, and/or other useful products.Type: ApplicationFiled: August 5, 2010Publication date: June 2, 2011Inventors: Joel R. Howard, Thomas E. Amidon, Shijie Liu, Christopher D. Wood
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Publication number: 20110054154Abstract: A thermoplastic material made from lignin, polyol and a melting point reducer where the melting point reducer is miscible in the specific polyol employed and where the lignin, polyol and melting point reducer are all miscible when in their melted state.Type: ApplicationFiled: August 31, 2009Publication date: March 3, 2011Applicant: Weyerhaeuser NR CompanyInventors: DAVID W. PARK, Amar N. Neogi, Ludwig Furtner, JR.
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Publication number: 20110028426Abstract: A process for dewatering biomass material comprising polysaccharide and water. The process comprises wetting the biomass material with a wetting composition comprising an alcohol to form a biomass slurry comprising wetted biomass material and a liquid component, mechanically separating a portion of the liquid component from the biomass slurry, and mechanically separating at least a portion of the water from the wetted biomass material. A process for extracting polysaccharide from the biomass material and a dewatered biomass material are also disclosed.Type: ApplicationFiled: July 28, 2009Publication date: February 3, 2011Applicant: CP KELCO APSInventors: Jens Eskil Trudsoe, Helle Bech Olsen, Mogens Andersen
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Publication number: 20110003352Abstract: A method for the fractionation of lignocellulosic materials into reactive chemical feedstock in a batch or semi continuous process by the stepwise treatment with aqueous aliphatic alcohols in the presence of sulfur dioxide or acid. Lignocellulosic material is fractionated in a fashion that cellulose is removed as pulp, or converted to esterified cellulose, cooking chemicals are reused, lignin is separated in the forms of reactive native lignin and reactive lignosulfonates and hemicelluloses are converted into fermentable sugars, while fermentation inhibitors are removed. In an integrated vapor compression stripper and evaporator system, aliphatic alcohol is removed from a liquid stream and the resulting stream is concentrated for further processing.Type: ApplicationFiled: June 12, 2007Publication date: January 6, 2011Applicant: AMERICAN PROCESS, INC.Inventors: Theodora Retsina, Vesa Pylkkanen, Rolf Ryham
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Publication number: 20100331531Abstract: Methods of making esterified lignocellulosic materials and resulting compositions and articles are disclosed.Type: ApplicationFiled: June 17, 2010Publication date: December 30, 2010Applicant: Eastman Chemical CompanyInventor: John Peter Mykytka
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Publication number: 20100305244Abstract: The present invention provides derivatives of native lignin having a certain aliphatic hydroxyl content. Surprisingly, it has been found that consistent and predictable antioxidant activity may be provided by selecting for derivatives of native lignin having a certain aliphatic hydroxyl content.Type: ApplicationFiled: February 15, 2010Publication date: December 2, 2010Inventors: Mikhail Yurevich Balakshin, Alex Berlin, Humbert Thomas Dellicolli, Chadrick Adam Nathaniel Jordan Grunert, Vera Maximenko Gutman, Darwin Ortiz, Edward Kendall Pye
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Publication number: 20100305242Abstract: The present invention provides hardwood derivatives of native lignin having a certain aliphatic hydroxyl content. Surprisingly, it has been found that consistent and predictable antioxidant activity may be provided by selecting for derivatives of native lignin having a certain aliphatic hydroxyl content.Type: ApplicationFiled: February 15, 2010Publication date: December 2, 2010Inventors: Mikhail Yurevich Balakshin, Alex Berlin, Humbert Thomas Dellicolli, Chadrick Adam Nathaniel Jordan Grunert, Vera Maximenko Gutman, Darwin Ortiz, Edward Kendall Pye
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Publication number: 20100305243Abstract: The present invention provides softwood derivatives of native lignin having a certain aliphatic hydroxyl content. Surprisingly, it has been found that consistent and predictable antioxidant activity may be provided by selecting for derivatives of native lignin having a certain aliphatic hydroxyl content.Type: ApplicationFiled: February 15, 2010Publication date: December 2, 2010Inventors: Mikhail Yurevich Balakshin, Alex Berlin, Humbert Thomas Dellicolli, Chadrick Adam Nathaniel Jordan Grunert, Vera Maximenko Gutman, Darwin Ortiz, Edward Kendall Pye
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Publication number: 20100249390Abstract: A new lignin degradation product, a method for producing the same, and methods for producing a saccharide raw material and a monosaccharide raw material are provided. The method for producing the new lignin degradation product includes: (a first step) mixing 100 parts by mass of a powder, obtained by pulverizing a lignocellulosic raw material and defatting the resulting powder with an organic solvent, with aqueous hydrogen peroxide in an amount of 20 to 400 parts by mass in terms of hydrogen peroxide and heating the mixture for 5 to 120 minutes at a pressure of 0.1 to 1.5 MPa and a temperature of 80 to 200° C. while irradiating the mixture with microwaves; (a second step) separating insoluble matter from the aqueous hydrogen peroxide; (a third step) extracting the insoluble matter with a solvent to produce an extract; and (a fourth step) distilling the solvent away from the extract to yield a solubilized lignin as a residue.Type: ApplicationFiled: October 15, 2008Publication date: September 30, 2010Applicant: NIPPON STEEL CHEMICAL CO., LTD.Inventors: Jun-ichi Azuma, Tetsuo Sakamoto, Kiyotaka Onishi
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Publication number: 20100136642Abstract: In one aspect, a process for treating woody plant material is provided, the process involving contacting the plant material with a continuous flow of an aqueous ethanol solution at elevated temperature and pressure under conditions that promote extraction of ethanol-soluble lignin from the plant material and retention of hemicellulose sugars, xylose and cellulose in the treated plant material solids. In another aspect, a process for extracting hemicellulose sugars from lignin-depleted plant material solids is provided, the process involving contacting lignin-depleted plant material with water at elevated temperature and pressure under conditions that promote extraction of hemicellulose sugars from the plant material; and recovering hemicellulose sugars from the liquid mixture.Type: ApplicationFiled: December 15, 2009Publication date: June 3, 2010Applicant: BIOJOULE LIMITEDInventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON, Clare ELTON, Alan McFARLANE, Mohammed Mehdi FARID, John CHEN
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Publication number: 20090069550Abstract: Lignin polymers having distinctive properties, including a generally high molecular weight and generally homogeneous size distribution, as well as preservation of native reactive side groups, are isolated by solvent extraction of plant materials. Methods for isolation of lignin polymers, and for use of the isolated lignin polymers are disclosed. Compositions containing lignin isolated from plant materials, such as carbon fiber composites, resins, adhesive binders and coatings, polyurethane-based foams, rubbers and elastomers, plastics, films, paints, nutritional supplements, food and beverage additives are disclosed. Xylose and xylose derivatives, furfural, fermentable sugars, cellulose and hemi-cellulose products may be used directly or further processed. The lignin polymers and other plant-derived products disclosed herein may be produced in abundance at low cost, and may be used as substitutes for feedstocks originating from fossil fuel or petrochemical sources in the manufacture of various products.Type: ApplicationFiled: September 2, 2008Publication date: March 12, 2009Applicant: BIOJOULE LIMITEDInventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON
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Publication number: 20090062516Abstract: Lignin polymers having distinctive properties, including a generally high molecular weight and generally homogeneous size distribution, as well as preservation of native reactive side groups, are isolated by solvent extraction of plant materials. Methods for isolation of lignin polymers, and for use of the isolated lignin polymers are disclosed. Compositions containing lignin isolated from plant materials, such as carbon fiber composites, resins, adhesive binders and coatings, polyurethane-based foams, rubbers and elastomers, plastics, films, paints, nutritional supplements, food and beverage additives are disclosed. Xylose and xylose derivatives, furfural, fermentable sugars, cellulose and hemi-cellulose products may be used directly or further processed. The lignin polymers and other plant-derived products disclosed herein may be produced in abundance at low cost, and may be used as substitutes for feedstocks originating from fossil fuel or petrochemical sources in the manufacture of various products.Type: ApplicationFiled: September 2, 2008Publication date: March 5, 2009Applicant: BIOJOULE LIMITEDInventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON
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Patent number: 6806356Abstract: A process for extracting secoisolariciresinol diglycoside (SDG) from de-fatted flaxseed is described. The process comprises contacting defatted flaxseed with an extraction solvent of acetone and water, extracting the de-fatted flaxseed with the extraction solvent to extract SDG-containing compounds, removal of solvents, followed by alkaline hydrolysis of the extract to liberate free SDG or its salts.Type: GrantFiled: April 2, 2003Date of Patent: October 19, 2004Assignee: Wiley Organics, Inc.Inventors: Thomas A. Dobbins, David B. Wiley
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Publication number: 20030216553Abstract: A process for extracting secoisolariciresinol diglycoside (SDG) from de-fatted flaxseed is described. The process comprises contacting defatted flaxseed with an extraction solvent of acetone and water, extracting the de-fatted flaxseed with the extraction solvent to extract SDG-containing compounds, removal of solvents, followed by alkaline hydrolysis of the extract to liberate free SDG or its salts.Type: ApplicationFiled: April 2, 2003Publication date: November 20, 2003Inventors: Thomas A. Dobbins, David B. Wiley
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Patent number: 6593460Abstract: The invention relates to biologically degradable lignin graft polymers comprised of lignin and ethylenically unsaturated monomers which are formed by an enzymatically catalyzed polymerization method in the presence of organic peroxides. The polymerizates are suited, for example, for utilization as absorbers for water and aqueous liquids, as coagulants and thickeners, as water softeners and as dispersing agents.Type: GrantFiled: October 12, 2000Date of Patent: July 15, 2003Assignee: Stockhausen GmbH & Co KGInventors: Aloys Hüttermann, Carsten Mai
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Publication number: 20030055227Abstract: Process for obtaining lignan from plant material by extraction with an extraction solvent and separation of the liquid fraction from the plant material. The separated liquid fraction containing the lignan product is subjected to further processing to remove cyanogenic sugars and other impurities. The resulting lignan containing product may be formulated for the treatment of various conditions, such as cancer, diabetes, hypertension, lupus, and atherosclerosis.Type: ApplicationFiled: March 20, 2002Publication date: March 20, 2003Inventors: Rishi Shukla, Ahmad K. Hilaly, Kevin M. Moore
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Patent number: 6335373Abstract: A novel process for the production of the natural antioxidant, carnosic acid, by extracting it from rosemary leaves with an aqueous solution of a lower alkyl alcohol in the presence of a water soluble acid is described. The extraction of the carnosic acid is very selective, i.e. very few other chemicals such as pro-oxidants from the plant are extracted. Furthermore, a method for the stabilization of the extracted acid from decomposition and a method of preparing the acid in high concentration are described.Type: GrantFiled: January 18, 2000Date of Patent: January 1, 2002Assignee: Lycored Natural Products Industries, Ltd.Inventors: Gil Ben-Yosef, Arkady Garbar
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Patent number: 6264853Abstract: A substanially pure chemically bound complex is derived from flax containing secoisolariciresinol diglucoside, cinnamic acid glycosides and hydroxy methyl glutaric acid. The complex is obtained by preparing an aqueous aliphatic alcoholic extract from flax and subjecting this aqueous extract to ultrafiltration whereby low molecular weight species remain with a filtrate and higher molecular weight species comprising the separated complex are retained.Type: GrantFiled: June 21, 1999Date of Patent: July 24, 2001Assignee: Agriculture and Agri-Food CanadaInventors: Neil D. Westcott, David Paton
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Patent number: 6239198Abstract: The invention proposes a process which enables separation of aromatic polymers which can be precipitated by acidification, as can be found especially in waste water from cellulose production, from an alkaline solution in a reliable manner and in pure form. To achieve good separation capacity, especially by filtration, it is proposed that the polymers be precipitated by reducing the pH at a relatively low temperature, typically between 15 and 60° C., and the dispersion be subsequently reheated until it passes into filterable form, typically between 50 and 95° C. The product separated in this way for example by filtration can be washed and can be dried at a high temperature, especially up to 110° C., without becoming black.Type: GrantFiled: September 1, 1999Date of Patent: May 29, 2001Assignee: Granit S.A.Inventors: Alfred Abächerli, Frank Doppenberg
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Patent number: 6072015Abstract: A method is provided for producing a painted article comprising: (a) preparing a lignin solution comprising lignin and a dye or pigment; (b) mixing the lignin solution with a phenol oxidizing enzyme; (c) incubating the mixture from said step (b) under conditions and for a time sufficient to form a solution of a desired viscosity; (d) contacting or spreading the mixture from the step (c) on an article to be painted; and (e) allowing the mixture to set onto the article by subjecting the article to conditions and for a time sufficient to form a paint on the surface of the article.Type: GrantFiled: December 8, 1998Date of Patent: June 6, 2000Assignee: Genencor International, Inc.Inventors: Rob Bolle, Wolfgang Aehle
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Patent number: 6054562Abstract: Lignin and polyether glycol produces a product which has a distinct melt point and melt viscosity. Polyether glycol has a plasticizing effect wherein the lignin can be thought of as the hard resin. When 20 parts of polyether glycol are processed with 80 parts of lignin a new material which has a melt point and a viscosity is created whereas lignin itself has no melt and flow characteristics. The new modified lignin can be cured with hexamine like a phenolic resin.Type: GrantFiled: February 25, 1999Date of Patent: April 25, 2000Inventor: Kenneth R. Kurple
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Patent number: 6013774Abstract: In this disclosure, there are provided materials which completely degrade in the environment far more rapidly than pure synthetic plastics but which possesses the desirable properties of a thermoplastic: strength, impact resistance, stability to aqueous acid or base, and deformation at higher temperatures. There is provided a method for using the degradable plastic materials in preparing strong, moldable solids. There is further provided a method of making and applications for macromolecular, surface active agents that change the wetting behavior of lignin-containing materials. These surface active agents are used to provide a method of making and applications for synthetic polymers coupled to pieces of a vascular plant using macromolecular surface active agents.Type: GrantFiled: September 29, 1998Date of Patent: January 11, 2000Inventors: John J. Meister, Meng-Jiu Chen
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Patent number: 5852069Abstract: In this disclosure, there are provided materials which completely degrade in the environment far more rapidly than pure synthetic plastics but which possesses the desirable properties of a thermoplastic: strength, impact resistance, stability to aqueous acid or base, and deformation at higher temperatures. There is provided a method for using the degradable plastic materials in preparing strong, moldable solids. There is further provided a method of making and applications for macromolecular, surface active agents that change the wetting behavior of lignin-containing materials. These surface active agents are used to provide a method of making and applications for synthetic polymers coupled to pieces of a vascular plant using macromolecular surface active agents.Type: GrantFiled: October 2, 1997Date of Patent: December 22, 1998Inventors: John J. Meister, Meng-Jiu Chen
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Patent number: 5756098Abstract: Methods and apparatus are provided for the recovery of organic compounds from fibrous plant materials. Organic compounds which can be recovered from the fibrous plant materials include plant metabolites, such as arabinogalactan and phenols, which can be isolated from the wood, for example, of the Western Larch and Tamarack tree varieties. In addition to the recovery of organic compounds from wood, fibrous wood products also may be isolated, in the form of a clean fiber that can be used, for example, as raw material in wood processing applications or in the manufacture of high quality paper products. In one embodiment, a fibrous plant material first is compressed, to recover a liquid exudate and a first pressed plant fiber product. Optionally, the fibrous plant material, such as wood particles, is compressed in the substantial absence of any added solvent, to produce a pure normal liquid exudate and a first pressed plant product.Type: GrantFiled: December 12, 1995Date of Patent: May 26, 1998Assignees: The University of Montana, Larex International, Inc., Crown Iron Works CompanyInventors: Christopher H. Price, Dale Hedtke, Geoffrey N. Richards, Michael S. Tempesta
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Patent number: 5741875Abstract: In this disclosure, there are provided materials which completely degrade in the environment far more rapidly than pure synthetic plastics but which possesses the desirable properties of a thermoplastic: strength, impact resistance, stability to aqueous acid or base, and deformation at higher temperatures. There is provided a method for using the degradable plastic materials in preparing strong, moldable solids. There is further provided a method of making and applications for macromolecular, surface active agents that change the wetting behavior of lignin-containing materials. These surface active agents are used to provide a method of making and applications for synthetic polymers coupled to pieces of a vascular plant using macromolecular surface active agents.Type: GrantFiled: March 8, 1995Date of Patent: April 21, 1998Inventors: John J. Meister, Meng-Jiu Chen
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Patent number: 5705618Abstract: A process is described for extracting lignans from flaxseed which comprises contacting a substantially oil-free flaxseed meal with an aliphatic alcohol solvent, e.g. a mixture of methanol or ethanol with water, to extract lignans into the alcohol solvent and separating residual solids from the lignan-rich alcohol solvent. The lignan-rich alcohol solvent is concentrated by removing solvent therefrom and the lignan concentrate obtained is subjected to a base-catalyzed hydrolysis to liberate lignans therefrom in a non-complexed form. Thereafter, the hydrolyzed concentrate is subjected to either a liquid/liquid partition, e.g. by an ethyl acetate/water system, or anion exchange to further enrich the lignans and the lignan-enriched solution thus obtained is subjected to chromatographic separation to isolate lignans at a purity of greater than 90 percent. The lignan, secoisolariciresinol diglucoside, was found in amounts of up to 20 mg per gram of defatted flaxseed.Type: GrantFiled: March 31, 1995Date of Patent: January 6, 1998Assignee: Agriculture and Agri-Food CanadaInventors: Neil D. Westcott, Alister D. Muir
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Patent number: 5484896Abstract: Individualized, esterified high lignin content cellulosic fibers containing intrafiber C.sub.2 -C.sub.9 polycarboxylic acid ester perform unexpectedly better in absorbent applications than lower lignin content esterified fibers from the same furnish.Type: GrantFiled: March 24, 1994Date of Patent: January 16, 1996Assignee: The Procter & Gamble CompanyInventors: Shahrokh A. Naieni, Carlisle M. Herron, Thomas R. Hanser
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Patent number: 5446133Abstract: A process for producing an oxidized lignosulfonate composition comprising admixing a lignosulfonate and nitric acid such that the amount of acid comprises from about 35% to about 100% by weight of dry solids of the lignosulfonate, and reacting said mixture for a time sufficient to form the oxidized lignosulfonate composition.Type: GrantFiled: March 2, 1994Date of Patent: August 29, 1995Assignee: LignoTech USA, Inc.Inventor: William J. Detroit
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Patent number: 5288857Abstract: The invention relates to a lignin preparation prepared from black liquor derived from an alkali delignification process, such as the sulphate process, soda process or polysulphide process. The lignin preparation comprises mainly lignin and at least the major part of the sodium content of the lignin separated from the black liquor deriving from such processes has been replaced with calcium, therewith to provide a lignin preparation having improved properties which render the preparation more suitable for use as fuel.Type: GrantFiled: February 16, 1993Date of Patent: February 22, 1994Assignee: Ligno Tech Sweden ABInventors: Wilhelm Aarsrud, Hans Bergstrom, Ingemar Falkehag
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Patent number: 5223258Abstract: An antiviral medicinal composition having spent liquor from kraft pulping and/or processed products thereof (kraft lignin, sulfomethylated and/or sulfopropylated kraft lignin) as major constituents, are effective agents in therapeutic and/or preventive methods against AIDS.Type: GrantFiled: January 11, 1990Date of Patent: June 29, 1993Assignee: Sanyo-Kokusaku Pulp Co., Ltd.Inventors: Makoto Machida, Makoto Yashiro, Kunichika Murakami
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Patent number: 5196460Abstract: A tackifier composition for use in rubber compounds is disclosed. The tackifier comprises a pure lignin with a water solubility of up to 1% by weight and a carbohydrate level of less than 50% by weight. In another embodiment of the invention, the pure lignin functions as both a tackifier and an antioxidant. In yet another preferred embodiment of the invention, the improved tackifier produces synergistic results when blended with a commercial tackifier, and the antioxidant likewise yields synergistic results when mixed with a commercial antioxidant.Type: GrantFiled: May 29, 1990Date of Patent: March 23, 1993Assignee: Repap Technologies Inc.Inventors: Jairo H. Lora, Michael J. Trojan, William H. Klingensmith
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Patent number: 5177169Abstract: Lignin, or a lignin derived material, which has been significantly demethylated (e.g., the demethylated lignin found in the raffinate produced as a by-product of dimethyl sulfide production which can be carried out using the spent liquor from wood pulping operations) can be isolated by a process wherein an organic solvent is added to a lignin-containing aqueous solution. The organic solvent is typically a polar, and at least a partially water-immiscible substance such as, for example, ethyl acetate. The resulting lignin-containing aqueous solution/organic solvent mixture is acidified to produce a water layer which is discarded and an organic solvent layer which contains the demethylated lignin. Upon its recovery, the demethylated lignin is dissolved in an alkaline solution to which an aldehyde source is added to produce a resol-type resin. The aldehyde source may be formaldehyde in solution, paraformaldehyde, hexamethylenetetramine, or other aldehydes including acetaldehyde, furfural, and their derivatives.Type: GrantFiled: May 29, 1991Date of Patent: January 5, 1993Assignee: Colorado State University Research FoundationInventor: Herbert A. Schroeder
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Patent number: 5116969Abstract: The invention is a very highly refined arabinogalactan gum falling within the molecular weight range of 6,000-2,500,000 and having a tannic acid equivalent of less than about 0.5 mg/g. The preferred product will have a molecular weight within the range of 6,000-1,300,000 and tannic acid equivalent no higher than about 0.25. The product is nearly colorless and is tasteless and odorless. it is prepared by first making a crude water extract of a natural source such as larch wood. This extract is next refined by the addition of an active MgO to precipitate the bulk of the lignans and iron containing compounds. Following that it is processed through a membrane no larger than about 0.45 .mu.m to remove any species having molecular weights in excess of about 2,500,000. The permeate may then be treated on successively smaller membranes down to about 6,000 daltons.Type: GrantFiled: April 26, 1990Date of Patent: May 26, 1992Assignee: Larex International, Inc.Inventors: Mark F. Adams, Melvin R. Knudson
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Patent number: 5102991Abstract: Lignin sulfonates are converted into sulfonic acid esters by blocking free phenolic hydroxyl groups on the lignin sulfonates from reaction with a suitable protective group, subjecting the blocked lignin sulfonate in aqueous solution to ion exchange to produce the free sulfonic acid thereof, exchanging the aqueous solvent into a polar organic solvent, such as isopropanol, and reacting the sulfonic acid derivative in the polar organic solvent with a saturated or unsaturated aliphatic epoxide, preferably an alkylene oxide. The resulting sulfonic acid ester adduct may be isolated and purified from the reactants using solvent extraction. Lignin sulfonic acid ester adducts are produced that are soluble in a variety of organic solvents and insoluble in water.Type: GrantFiled: April 11, 1990Date of Patent: April 7, 1992Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Wolfgang Glasser, Kaliprasanna Dhara
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Patent number: 5026808Abstract: Lignin, or a lignin derived material, which has been significantly demethylated (e.g., the demethylated lignin found in the raffinate produced as a by-product of dimethyl sulfide production which can be carried out using the spent liquor from wood pulping operations) can be isolated by a process wherein an organic solvent is added to a lignin-containing aqueous solution. The organic solvent is typically a polar, and at least a partially water-immiscible substance such as, for example, ethyl acetate. The resulting lignin-containing aqueous solution/organic solvent mixture is acidified to produce a water layer which is discarded and an organic solvent layer which contains the demethylated lignin. Upon its recovery, the demethylated lignin is dissolved in an alkaline solution to which an aldehyde source is added to produce a resol-type resin. The aldehyde source may be formaldehyde in solution, paraformaldehyde, hexamethylenetetramine, or other aldehydes including acetaldehyde, furfural, and their derivatives.Type: GrantFiled: April 3, 1989Date of Patent: June 25, 1991Assignee: Colorado State University Research FoundationInventor: Herbert A. Schroeder
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Patent number: 5021531Abstract: Lignin, or a lignin derived material, which has been significantly demethylated (e.g., the demethylated lignin found in the raffinate produced as a by-product of dimethyl sulfide production which can be carried out using the spent liquor from wood pulping operations) can be isolated by a process wherein an organic solvent is added to a lignin-containing aqueous solution. The organic solvent is typically a polar, and at least a partially water-immiscible substance such as, for example, ethyl acetate. The resulting lignin-containing aqueous solution/organic solvent mixture is acidified to produce a water layer which is discarded and an organic solvent layer which contains the demethylated lignin. Upon its recovery, the demethylated lignin is preferably dried and stored until it is used (along with an alkali, an aldehyde and an adhesive filler) in compounding an adhesive of the type generally used in the manufacture of plywood.Type: GrantFiled: February 20, 1990Date of Patent: June 4, 1991Assignee: Colorado State University Research FoundationInventor: Herbert A. Schroeder
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Patent number: 5010156Abstract: A lignin-modified phenol-formaldehyde resin for use as an adhesive for particulate wood products is disclosed which is prepared by reacting phenol and formaldehyde with an aqueous alkaline solution of an organosolv lignin. The organosolv lignin used in the formation of the resin is obtained from a pulping liquor prepared from particulate wood material from hardwood trees, aqueous polar organic solvent, and an acid catalyst. The resin allows for replacement of phenol or organosolv lignin at a level of up to 40% without detrimentally affecting its performance in terms of bonding strength or durability. The resin of the present invention is also superior to prior art lignin-modified resins in that it is low in sulfate, ash and sulfur residues, and thus will not give off distracting or harmful sulfur odors during resin preparation or hot-pressing of the adhesive and is unaffected and not solubilized by water.Type: GrantFiled: March 12, 1990Date of Patent: April 23, 1991Assignee: Eastman Kodak CompanyInventors: Phillip M. Cook, Steven L. Hess
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Patent number: 4966650Abstract: The chemical components of lignocellulosic material which have been dissociated by a steam explosion process can be extracted from the mixture of components using a solvent extraction process. The solvents are water, alcohol and a mild caustic in that order, or the alcohol step can be by-passed and only water and caustic are used. The caustic is a stronger solvent and it will extract the alcohol solubles along with the caustic only solubles. The eluant from the these extractions contains a range of lignin derived substances, which have different applications, such as thermoplastic and thermosetting characteristics. This invention describes a method for partitioning these lignin components into reproducible fractions having definable characteristics for particular applications. For instance, many copolymer applications require a thermosetting only fraction of the lignin. Other applications require a thermoplastic only lignin.Type: GrantFiled: September 19, 1988Date of Patent: October 30, 1990Inventors: Edward A. DeLong, George S. Ritchie
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Patent number: 4908098Abstract: The chemical components of lignocellulosic material that have been dissociated by a stream explosion process can be extracted from the mixture of components using a solvent extraction process. The dissociated lignocellulosic material is put in a column and the substances which are soluble in water, alcohol and caustic are leached out of the mixture by solvent extraction with relatively small volumes of those solvents. No agitation is used. Substantially pure cellulose remains in the column and it can be bleached before removal from the column.Type: GrantFiled: April 18, 1989Date of Patent: March 13, 1990Assignee: Tigney Technology Inc.Inventors: Edward A. DeLong, Edward P. DeLong, George S. Ritchie, W. Alan Rendall
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Patent number: 4826566Abstract: A method of rapidly and efficiently treating ligno-cellulosic material for removal of lignin and other non-carbohydrates as well as non-cellulosic carbohydrates from cellulosic matter. Such material is first impregnated with a liquor which is a reaction product obtained by mixing triethyleneglycol with an arylsulfonic or other organic acid. The impregnated material is then rapidly heated by microwaving or application of rf energy to a temperature between about 119 degrees Centigrade to 130 degrees Centigrade and maintained at that temperature for only two to five minutes to reduce the effects of hydrolysis. Thereafter, conventional filtration and washing techniques are applied to achieve a residue material suitable for further use as a wood pulp or for further hydrolysis for the production of organic chemicals.Type: GrantFiled: January 11, 1988Date of Patent: May 2, 1989Assignee: Le Tourneau CollegeInventor: Leonard F. Burkart
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Patent number: 4764596Abstract: Lignin is precipitated in high yields and at high rates from a black liquor produced by pulping wood at high temperatures and pressures with an aqueous lower aliphatic alcohol solvent. The lignin is precipitated by diluting the black liquor with water and an acid to form a solution with a pH of less than about 3, an alcohol content of less than about 30% by volume and a temperature of less than about 75.degree. C. The precipitated lignin, when subsequently dried, is in the form of a powder which requires little or no crushing to convert it into a fine uniform size suitable for use without further significant processing.Type: GrantFiled: December 11, 1986Date of Patent: August 16, 1988Assignee: Repap Technologies Inc.Inventors: Jairo H. Lora, Raphael Katzen, Malcolm Cronlund, Chih F. Wu
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Patent number: 4728727Abstract: The present invention relates to modified lignosulfonate materials and the process for their preparation. These modified lignosulfonates result from the sulfonation of ultrafiltered lignosulfonates by reaction with sulfite-bisulfite salts. The removal of sugars and other low molecular weight impurities makes formation of these new modified lignosulfonates more complete. These derivative materials when reacted with metal salts such as chromium, ferrous, ferric, titanium, and zirconium produce oil well drilling fluid dispersant products with significantly improved performance and thermal properties.Type: GrantFiled: January 28, 1987Date of Patent: March 1, 1988Assignee: ITT CorporationInventors: Marten Reintjes, Craig D. Marken
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Patent number: 4493797Abstract: An autoclave extraction apparatus using supercritical fluid is used for supercritical fluid extraction of one or several compounds. The supercritical fluid containing the compound(s) may then be processed in a pressurized bed reactor under supercritical conditions. The bed being a fluidizable catalytic bed to carry out a catalytic reaction of the compound(s).The method is particularly applicable to recover valuable lignin and other extractable components from kraft black liquor.Type: GrantFiled: December 22, 1983Date of Patent: January 15, 1985Inventor: Michael M. Avedesian